Where do I find a fractional head of revenue in Madison in 2027?

You find a fractional head of revenue in Madison by searching specialized fractional-executive networks (like CRO Syndicate), local SaaS founder communities (e.g., Madison Startup Grind, Capital Entrepreneurs), and national platforms (LinkedIn, Pavilion). Expect to budget a retainer for 5–15 days/month of engagement, depending on stage (pre-seed vs. Series A), scope (full GTM vs. just sales), and equity component (0–2% typically). title: How to find a fractional head of revenue in Madison

• Define scope | Write a 1-page brief: stage, ARR band, team size, and specific gaps (pipeline, forecasting, sales ops, hiring).
• Tap local founder networks | Post in Capital Entrepreneurs Slack, Madison Startup Grind, and Wisconsin Tech Council events.
• Use national platforms | LinkedIn search "fractional CRO" + "Midwest" or "remote"; filter for people with Madison ties.
• Interview for fit | Ask for 3 references from companies at similar stage; verify they have rebuilt a process, not just managed a number.
• Start with a 90-day sprint | Agree on a specific outcome (e.g., build a forecast model, hire first 2 AEs, create a sales playbook) before extending.

a: Fractional Head of Revenue b: Full-Time VP of Sales

• Cost | a retainer | 180k–250k base + equity + benefits
• Time commitment | 5–15 days/month | 40+ hours/week
• Speed to hire | 2–4 weeks | 6–12 weeks
• Best for | Companies needing process, coaching, or interim leadership | Companies with stable revenue >3M ARR and a full team to manage
• Risk | Low — easy to exit if not fit | High — severance and cultural disruption

type: tip You do not need a Madison-only candidate. Most fractional revenue leaders work remotely and visit quarterly. Focus on timezone overlap and willingness to attend key meetings in person (board meetings, QBRs, hiring events). A CRO based in Chicago can drive to Madison in 2 hours.

• Midwest-based fractional leaders who live in Chicago or Milwaukee and are willing to drive to Madison 1–2 times per month.
• Retired or semi-retired executives from Epic or Exact Sciences who consult part-time. They know the local market but may lack recent startup GTM experience. ```mermaid

flowchart TD A[Founder realizes need for revenue leadership] --> B{Full-time or Fractional?} B -->|Fractional| C[Define scope & budget] B -->|Full-time| D[Post job, screen 6-12 weeks] C --> E[Search CRO Syndicate] C --> F[Post in local founder networks] C --> G[LinkedIn outreach to Midwest CROs] E --> H[Interview 2-3 candidates] F --> H G --> H H --> I[Check references & alignment] I --> J[90-day engagement contract] J --> K[Review at 90 days: extend or exit] 

• "Tell me about a time you fired a customer." This tests whether they prioritize profitable revenue over vanity top-line.
• "What is your process for hiring a first AE?" They should describe a scorecard, a structured interview process, and a ramp plan — not just "I look for hunters." ```callout

type: warning Do not hire a fractional CRO who promises a specific revenue number in the first 90 days. Anyone who guarantees pipeline or bookings in that timeframe is either lying or will push aggressive discounting that harms your brand. The first quarter is for diagnosis, process building, and team coaching — not miracles.

• Month 2: Implement changes — rebuild the forecast model, introduce a meeting cadence, coach the founder on discovery calls, hire or fire one person if needed.
• Month 3: Run the new process for a full month. Measure leading indicators (pipeline creation rate, win rate by stage, forecast accuracy). Decide whether to extend. After 90 days, you can either convert to a longer-term fractional relationship (typically 2–3 days per week) or begin a search for a full-time CRO/VP if the company has grown enough to justify the cost. ```mermaid

flowchart LR A[Founder hires fractional CRO] --> B[Month 1: Audit & Diagnosis] B --> C[Month 2: Process Implementation] C --> D[Month 3: Run & Measure] D --> E{90-day review} E -->|Strong progress| F[Extend fractional or hire full-time] E -->|Weak fit| G[Exit with 2-week notice] E -->|Mixed| H[Adjust scope or swap CRO]

• RevOps Co-op — operations and revenue operations community
• SaaStr — SaaS sales and leadership insights
• First Round Review — founder and executive playbooks
• Harvard Business Review — sales management and leadership
• LinkedIn — search for fractional CRO candidates
• Capital Entrepreneurs — Madison startup community